Both monolingual and English resources on “〜といい” indicate it means “should” or “hope that” similar to “〜たほうがいい” but I often see sentences like say “何でも好きなものを注文するといい” where it seems to not so much indicate that it's better for the listener to order whatever he likes, but that he has permission to do so, from the person who will pay for it but no literature seems to cover this usage, so am I wrong?
3 Answers
Should can be a bit of a problematic word in English. Is it an instruction (similar to a command), a recommendation, or even merely a suggestion?
If I read a particular book, really enjoyed it, and thought my friend would enjoy reading it too, I might say, "You should read this." I'm not telling them what they have to do.
In a restaurant, looking at a menu, someone might encourage you,
何でも好きなものを注文するといい
You should order whatever you'd like.
Without any further context, there's no reason to conclude permission is being granted here.
In your question, you say, "it seems to not so much indicate that it's better for the listener to order whatever he likes..." I want to focus on the word better here. いい here would not indicate something is better than something else unless you seem some sort of comparison going on such as "...ほう" or "...より". Otherwise, いい just has the sense of English "it's OK" with all the ambiguity that "OK" might convey. (Of course, without seeing how those monolingual and English resources explain this grammatical structure, it's a bit hard to adequately comment on this point.)
I think it would be good to keep in mind that English should isn't always a directive about what one must do, it can be a suggestion or even encouragement (particularly in a context where one might hesitate, such as when someone else is paying). It is with this later sense that you should understand this usage of といい.
~するといい indicats "suggestion" rather than "permission".
~するといい means like "I think that it is good for you to do ~."
いい is the spoken form of よい, and よい has many meanings, such as good, right, correct, enough, wealthy, healthy, prepared, preferable, comfortable, and acceptable.
In your example, よい or いい can be ambiguous, as it may indicate either permission, recommendation, or just a comment. This ambiguity could be the cause of confusion or arguments.
When someone says ‘何でも好きなものを注文するといい,’ the listener is likely to expect that the speaker will pay for it. However, depending on the person or situation, it doesn’t necessarily mean they will pay and they might say "おごるなんて一言も言ってない / I never said I’d pay for it" after the meal. In reality, the listener will reply to the speaker something like "おごってくれるんですか? / Are you going to pay for my meal?" or "ごちそうさまです。 / Thank you for the meal in advance."